Methyl chloroformate → HCID 68464317, compound

HRID 501216Notes

Reaction equation

HRID 501216 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11]2[C:14]3[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=3[O:16][C:10]=2[CH2:9]1)C1C=CC=CC=1.Cl[C:22]([O:24][CH3:25])=[O:23]>ClC(Cl)C>[CH2:9]1[C:10]2[O:16][C:15]3[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=3[C:11]=2[CH2:12][CH2:13][N:8]1[C:22]([O:24][CH3:25])=[O:23]

Participants

4

Reactant 2

HCID 6586Methyl chloroformateHCID 13925234HCID 13925234, compound

Product 1

HCID 68464317HCID 68464317, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A mixture of 2-benzyl-1,2,3,4-tetrahydro[1]benzofuro[2,3-c]pyridine (0.2 g, 0.75 mmol) and methyl chloroformate (0.358 g, 3.787 mmol) in dichloroethane (15 mL) was refluxed for 1 h. The reaction mixture was cooled to room temperature and washed with saturated NaHCO3 (25 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated to furnish methyl 3,4-dihydro[1]benzofuro[2,3-c]pyridine-2(1H)-carboxylate (0.150 g, 85.7%). 1H NMR (200 MHz, CDCl3): δ 2.70-2.76 (m, 2H), 3.80 (s, 5H), 4.72 (m, 2H), 7.22 (m, 2H), 7.42 (m, 2H).

Workup

  1. temperaturewas refluxed for 1 h
  2. washwashed with saturated NaHCO3 (25 mL)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-55e9736b7e854fb9af90bdd2a3eab78f
Source dataset
uspto-grants-2010_08
Patent number
US07772245B2

Reaction notes

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